CA2232626C - Nouveaux ligands a affinite et leur utilisation - Google Patents
Nouveaux ligands a affinite et leur utilisation Download PDFInfo
- Publication number
- CA2232626C CA2232626C CA2232626A CA2232626A CA2232626C CA 2232626 C CA2232626 C CA 2232626C CA 2232626 A CA2232626 A CA 2232626A CA 2232626 A CA2232626 A CA 2232626A CA 2232626 C CA2232626 C CA 2232626C
- Authority
- CA
- Canada
- Prior art keywords
- group
- affinity ligand
- matrix
- general formula
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000003446 ligand Substances 0.000 title claims abstract description 168
- 239000011159 matrix material Substances 0.000 claims abstract description 169
- 238000000746 purification Methods 0.000 claims abstract description 45
- 239000002243 precursor Substances 0.000 claims abstract description 34
- 102000004877 Insulin Human genes 0.000 claims abstract description 32
- 108090001061 Insulin Proteins 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 25
- 108060003951 Immunoglobulin Proteins 0.000 claims abstract description 23
- 102000018358 immunoglobulin Human genes 0.000 claims abstract description 23
- 229940072221 immunoglobulins Drugs 0.000 claims abstract description 18
- 239000004026 insulin derivative Substances 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 239000012634 fragment Substances 0.000 claims abstract description 16
- 102100023804 Coagulation factor VII Human genes 0.000 claims abstract description 12
- 108010023321 Factor VII Proteins 0.000 claims abstract description 12
- 229940012413 factor vii Drugs 0.000 claims abstract description 12
- 102000002265 Human Growth Hormone Human genes 0.000 claims abstract description 11
- 108010000521 Human Growth Hormone Proteins 0.000 claims abstract description 11
- 239000000854 Human Growth Hormone Substances 0.000 claims abstract description 11
- 125000006850 spacer group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 66
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical class N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 50
- 229920000936 Agarose Polymers 0.000 claims description 47
- 102000004169 proteins and genes Human genes 0.000 claims description 45
- 108090000623 proteins and genes Proteins 0.000 claims description 45
- -1 sulphamoyl groups Chemical group 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000003277 amino group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
- 238000001042 affinity chromatography Methods 0.000 claims description 17
- 229940027941 immunoglobulin g Drugs 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 230000027455 binding Effects 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 238000002955 isolation Methods 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000003213 activating effect Effects 0.000 claims description 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 229920000620 organic polymer Polymers 0.000 claims description 10
- 238000012512 characterization method Methods 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000011002 quantification Methods 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910044991 metal oxide Inorganic materials 0.000 claims description 8
- 150000004706 metal oxides Chemical class 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 150000001720 carbohydrates Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 229920001282 polysaccharide Polymers 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
- 229920002307 Dextran Polymers 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- XFXOLBNQYFRSLQ-UHFFFAOYSA-N 3-amino-2-naphthoic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(N)=CC2=C1 XFXOLBNQYFRSLQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229940099472 immunoglobulin a Drugs 0.000 claims description 5
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 claims description 4
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000006143 cell culture medium Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 108010013773 recombinant FVIIa Proteins 0.000 claims 1
- 229940068953 recombinant fviia Drugs 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 96
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 82
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 57
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 229960003732 tyramine Drugs 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 229940125396 insulin Drugs 0.000 description 29
- 238000004458 analytical method Methods 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- 238000004007 reversed phase HPLC Methods 0.000 description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- 239000001508 potassium citrate Substances 0.000 description 16
- 229960002635 potassium citrate Drugs 0.000 description 16
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 16
- 235000011082 potassium citrates Nutrition 0.000 description 16
- 239000000872 buffer Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 11
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 11
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- RQJDUEKERVZLLU-UHFFFAOYSA-N 4-Hydroxybenzylamine Chemical compound NCC1=CC=C(O)C=C1 RQJDUEKERVZLLU-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010828 elution Methods 0.000 description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- 101000976075 Homo sapiens Insulin Proteins 0.000 description 8
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 8
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 229960004050 aminobenzoic acid Drugs 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
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- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
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- 229940088598 enzyme Drugs 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 4
- QXMZOACRAXAUJP-UHFFFAOYSA-N 5-aminonaphthalen-1-ol;3-aminophenol Chemical compound NC1=CC=CC(O)=C1.C1=CC=C2C(N)=CC=CC2=C1O QXMZOACRAXAUJP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 101800002416 Insulin B chain' Proteins 0.000 description 4
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Classifications
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
- B01J20/3255—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. heterocyclic or heteroaromatic structures
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3289—Coatings involving more than one layer of same or different nature
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—Insulins
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6854—Immunoglobulins
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/58—Use in a single column
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Cell Biology (AREA)
- Physics & Mathematics (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Endocrinology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- Diabetes (AREA)
- Inorganic Chemistry (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Peptides Or Proteins (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cette invention a trait à de nouveaux conjugués ligand à affinité-matrice comportant un ligand de la formule générale (a). Ce ligand est rattaché à une matrice de support en position A, éventuellement par le biais d'un bras d'espacement s'interposant entre la matrice et le ligand. Cette invention porte, en outre, sur ces nouveaux conjugués ligand à affinité-matrice, sur leur préparation et leur utilisation dans le cadre de la purification de matières protéiniques telles que des immunoglobulines, des insulines, le facteur VII ou l'hormone de croissance humaine, par exemple, ou bien de leurs analogues, dérivés et fragments et précurseurs.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9519197.9 | 1995-09-20 | ||
| GBGB9519197.9A GB9519197D0 (en) | 1995-09-20 | 1995-09-20 | Novel affinity ligands and their use |
| PCT/DK1996/000399 WO1997010887A1 (fr) | 1995-09-20 | 1996-09-19 | Nouveaux ligands a affinite et leur utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2232626A1 CA2232626A1 (fr) | 1997-03-27 |
| CA2232626C true CA2232626C (fr) | 2011-11-29 |
Family
ID=10780990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2232626A Expired - Lifetime CA2232626C (fr) | 1995-09-20 | 1996-09-19 | Nouveaux ligands a affinite et leur utilisation |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0959975B1 (fr) |
| JP (1) | JP4824147B2 (fr) |
| KR (1) | KR100537386B1 (fr) |
| CN (1) | CN1089617C (fr) |
| AR (1) | AR003634A1 (fr) |
| AT (1) | ATE285827T1 (fr) |
| AU (1) | AU702901B2 (fr) |
| CA (1) | CA2232626C (fr) |
| DE (1) | DE69634142T2 (fr) |
| DK (1) | DK0959975T3 (fr) |
| ES (1) | ES2236748T3 (fr) |
| GB (1) | GB9519197D0 (fr) |
| MY (1) | MY127957A (fr) |
| RU (1) | RU2175261C2 (fr) |
| WO (1) | WO1997010887A1 (fr) |
| ZA (1) | ZA967917B (fr) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5760187A (en) * | 1996-02-22 | 1998-06-02 | Mitsui Toatsu Chemicals, Inc. | Purification process of a human growth hormone |
| CA2876986C (fr) * | 1996-08-30 | 2017-08-29 | Dpx Holdings B.V. | Isolement d'immunoglobulines |
| EP0945447A1 (fr) * | 1998-03-27 | 1999-09-29 | Janssen Pharmaceutica N.V. | Dérivés de 1,3,5-triazine trisubstituées pour le traitement de l'infection par le VIH |
| GB9910807D0 (en) | 1999-05-10 | 1999-07-07 | Prometic Biosciences Limited | Novel detoxification agents and their use |
| SK285240B6 (sk) | 1999-09-24 | 2006-09-07 | Janssen Pharmaceutica N. V. | Antivírusové prostriedky |
| US6153365A (en) | 1999-12-16 | 2000-11-28 | Eastman Kodak Company | Photographic processing compositions containing stain reducing agent |
| US6153364A (en) * | 1999-12-16 | 2000-11-28 | Eastman Kodak Company | Photographic processing methods using compositions containing stain reducing agent |
| CA2407276A1 (fr) | 2000-04-28 | 2001-11-08 | Accurate Polymers, Ltd. | Activite simulee de proteine a presentee par de petits ligands fixes a une surface de perle de cellulose |
| US6440651B1 (en) | 2000-10-05 | 2002-08-27 | Eastman Kodak Company | Concentrated photographic fixer additive and fixing compositions and method of photographic processing |
| US6288227B1 (en) * | 2000-10-05 | 2001-09-11 | Eastman Kodak Company | Solublized 2,6-dinaphthylaminotriazines |
| US6943162B2 (en) | 2001-01-26 | 2005-09-13 | Smithkline Beecham Corporation | Piperazinyltriazines as estrogen receptor modulators |
| US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
| GB0224446D0 (en) * | 2002-10-21 | 2002-11-27 | Univ Cambridge Tech | Affinity adsorbents for immunoglobulins |
| GB0228724D0 (en) | 2002-12-09 | 2003-01-15 | Prometic Biosciences Ltd | Multidimensinal libraries |
| US7109040B2 (en) * | 2002-12-13 | 2006-09-19 | Agilent Technologies, Inc. | Modular isotope coding approach to proteomic analysis |
| US7700743B2 (en) | 2003-07-22 | 2010-04-20 | Millipore Corporation | Immobilised affinity medium and its use in separation |
| US7750129B2 (en) | 2004-02-27 | 2010-07-06 | Ge Healthcare Bio-Sciences Ab | Process for the purification of antibodies |
| SE0400501D0 (sv) * | 2004-02-27 | 2004-02-27 | Amersham Biosciences Ab | Antibody purification |
| SE0401665D0 (sv) * | 2004-06-24 | 2004-06-24 | Amersham Biosciences Ab | Purification of immunoglobulins |
| GB0416699D0 (en) * | 2004-07-27 | 2004-09-01 | Prometic Biosciences Ltd | Prion protein ligands and methods of use |
| AU2005279615A1 (en) * | 2004-09-03 | 2006-03-09 | Prometic Biosciences Inc. | 2,4,6-triamino-s-triazine-based compounds which bind to the tail (Fc) portion of immunoglobulins and their use |
| BRPI0518216C8 (pt) * | 2004-10-21 | 2017-03-21 | Ge Healthcare Bio Sciences Ab | ligante de cromatografia, métodos de preparação de uma matriz de separação, e de separação de um ou mais anticorpos de um ou mais outros compostos em uma amostra líquida, matriz de separação, e, coluna de cromatografia descartável. |
| WO2006067230A1 (fr) | 2004-12-23 | 2006-06-29 | Novo Nordisk Health Care Ag | Reduction du contenu en contaminants proteiques de compositions renfermant une proteine d'interet dependante de la vitamine k |
| AU2005318700B2 (en) * | 2004-12-23 | 2011-04-14 | Novo Nordisk A/S | Antibody binding affinity ligands |
| GB0509443D0 (en) * | 2005-05-09 | 2005-06-15 | Prometic Biosciences Ltd | Affinity adsorbents for factor VIII and von willebrand's factor |
| GB0509438D0 (en) * | 2005-05-09 | 2005-06-15 | Prometic Biosciences Ltd | Affinity adsorbets for fibrinogen |
| GB0509442D0 (en) * | 2005-05-09 | 2005-06-15 | Prometic Biosciences Ltd | Affinity adsorbents for fibrinogen |
| US8501939B2 (en) | 2005-06-10 | 2013-08-06 | Prometic Biosciences Limited | Triazines and pyrimidines as protein binding ligands |
| US20080220968A1 (en) * | 2005-07-05 | 2008-09-11 | Ge Healthcare Bio-Sciences Ab | [1, 2, 4] Triazolo [1, 5-A] Pyrimidine Derivatives as Chromatographic Adsorbent for the Selective Adsorption of Igg |
| GB0604236D0 (en) | 2006-03-02 | 2006-04-12 | Prometic Biosciences Ltd | Adsorbents for protein purification |
| ES2616982T3 (es) | 2007-03-28 | 2017-06-15 | Patheon Holdings I B.V. | Columna de lecho expandido y cromatografía desechable |
| CN101679321B (zh) * | 2007-04-30 | 2012-10-03 | 普罗米蒂克生物科学公司 | 三嗪衍生物、含所述衍生物的组合物以及所述衍生物在制备用于治疗癌症和自身免疫性疾病药物中的应用 |
| GB0808908D0 (en) * | 2008-05-16 | 2008-06-25 | Avecia Biolog Ltd | Purification process |
| ES2645689T5 (en) | 2008-05-21 | 2025-06-24 | Takeda Pharmaceuticals Co | Phosphorous derivatives as kinase inhibitors |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| CN102216325A (zh) * | 2008-11-13 | 2011-10-12 | 诺沃-诺迪斯克有限公司 | 使用包括特异性配体的亲和树脂用于纯化人生长激素多肽的方法 |
| ES2764100T3 (es) | 2009-04-15 | 2020-06-02 | Abraxis Bioscience Llc | Composiciones de nanopartículas exentas de priones y métodos |
| EP2427489B1 (fr) * | 2009-05-07 | 2015-04-22 | Novozymes Biopharma DK A/S | Procédé pour limiter la glycosylation à liaison o des anticorps |
| CN102498110A (zh) | 2009-06-10 | 2012-06-13 | 雅培制药有限公司 | 作为激酶抑制剂的2-(lh-吡唑-4-基氨基)-嘧啶 |
| KR101866265B1 (ko) * | 2009-07-28 | 2018-06-11 | 인스트랙션 게엠베하 | 단백질 및 펩타이드 결합용 특정 흡착제, 및 이를 사용하는 분리방법 |
| US8952150B2 (en) | 2009-09-23 | 2015-02-10 | Albert Einstein College Of Medicine Of Yeshiva University | Prostaglandin transporter inhibitors and uses thereof |
| US9273151B2 (en) | 2011-03-24 | 2016-03-01 | Kaneka Corporation | Proteinaceous-substance-binding low-molecular-weight compound |
| KR101884010B1 (ko) | 2011-05-04 | 2018-07-31 | 어리어드 파마슈티칼스, 인코포레이티드 | Egfr-유도된 암의 세포 증식을 억제하는 화합물 |
| JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Egfr発動性がんの細胞増殖阻害用化合物 |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| GB2513405A (en) | 2013-04-26 | 2014-10-29 | Adc Biotechnology Ltd | Method of synthesising ADCs using affinity resins |
| CN104148018B (zh) * | 2013-05-14 | 2018-04-20 | 上海亨臻实业有限公司 | 抗体亲和纯化材料及其用途 |
| EP2918641A1 (fr) | 2014-03-13 | 2015-09-16 | Basf Se | Procédé de purification d'anticorps, fragments d'anticorps ou leurs variants manipulés à l'aide de structures ligands colorants d'anthraquinone spécifiques |
| GB201419184D0 (en) | 2014-10-28 | 2014-12-10 | Adc Biotechnology Ltd | Method of synthesising biomolecule-effector/reporter-conjugates using affinity resins |
| GB201419185D0 (en) | 2014-10-28 | 2014-12-10 | Adc Biotechnology Ltd | Method of synthesising ADCs using affinity resin |
| RU2627849C1 (ru) * | 2016-07-22 | 2017-08-14 | Игорь Анатольевич Мнушкин | Способ разделения газового потока на отдельные компоненты или фракции |
| RU2626354C9 (ru) * | 2016-07-25 | 2017-10-04 | Игорь Анатольевич Мнушкин | Способ разделения газового потока на отдельные компоненты или фракции |
| CN109354600B (zh) * | 2018-11-29 | 2021-08-10 | 浙江海洋大学 | 一种牛磺酸修饰的新型阿拉斯加鳕鱼多功能肽的制备方法 |
| CN113527284B (zh) * | 2021-07-16 | 2024-08-06 | 东莞市顶盛环保科技有限公司 | 一种含双酯基均三嗪衍生物的环保多功能材料及其制备方法与应用 |
| CN113563324B (zh) * | 2021-07-22 | 2024-08-06 | 东莞市顶盛环保科技有限公司 | 一种含酯基均三嗪的绿色环保多功能材料及其制备方法与应用 |
| CN118719009B (zh) * | 2024-07-18 | 2025-02-14 | 山东微领生物有限公司 | 一种层析介质改性方法 |
Family Cites Families (1)
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| DE3726019A1 (de) * | 1987-08-05 | 1989-02-16 | Boehringer Mannheim Gmbh | Verfahren zur abtrennung und reinigung von t-pa |
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1995
- 1995-09-20 GB GBGB9519197.9A patent/GB9519197D0/en active Pending
-
1996
- 1996-09-18 MY MYPI96003852A patent/MY127957A/en unknown
- 1996-09-19 DE DE69634142T patent/DE69634142T2/de not_active Expired - Lifetime
- 1996-09-19 CA CA2232626A patent/CA2232626C/fr not_active Expired - Lifetime
- 1996-09-19 ES ES96930037T patent/ES2236748T3/es not_active Expired - Lifetime
- 1996-09-19 JP JP51233597A patent/JP4824147B2/ja not_active Expired - Lifetime
- 1996-09-19 EP EP96930037A patent/EP0959975B1/fr not_active Expired - Lifetime
- 1996-09-19 AU AU69242/96A patent/AU702901B2/en not_active Expired
- 1996-09-19 CN CN96197849A patent/CN1089617C/zh not_active Expired - Lifetime
- 1996-09-19 RU RU98107896/12A patent/RU2175261C2/ru not_active IP Right Cessation
- 1996-09-19 KR KR1019980702097A patent/KR100537386B1/ko not_active Expired - Fee Related
- 1996-09-19 DK DK96930037T patent/DK0959975T3/da active
- 1996-09-19 WO PCT/DK1996/000399 patent/WO1997010887A1/fr not_active Ceased
- 1996-09-19 ZA ZA967917A patent/ZA967917B/xx unknown
- 1996-09-19 AT AT96930037T patent/ATE285827T1/de active
- 1996-09-20 AR ARP960104427A patent/AR003634A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP0959975B1 (fr) | 2004-12-29 |
| AU6924296A (en) | 1997-04-09 |
| MY127957A (en) | 2007-01-31 |
| DK0959975T3 (da) | 2005-05-09 |
| ATE285827T1 (de) | 2005-01-15 |
| CN1200680A (zh) | 1998-12-02 |
| CN1089617C (zh) | 2002-08-28 |
| AU702901B2 (en) | 1999-03-11 |
| AR003634A1 (es) | 1998-08-05 |
| JPH11512442A (ja) | 1999-10-26 |
| GB9519197D0 (en) | 1995-11-22 |
| KR19990063645A (ko) | 1999-07-26 |
| RU2175261C2 (ru) | 2001-10-27 |
| WO1997010887A1 (fr) | 1997-03-27 |
| EP0959975A1 (fr) | 1999-12-01 |
| DE69634142T2 (de) | 2005-12-29 |
| CA2232626A1 (fr) | 1997-03-27 |
| ES2236748T3 (es) | 2005-07-16 |
| KR100537386B1 (ko) | 2006-04-21 |
| ZA967917B (en) | 1997-03-20 |
| DE69634142D1 (de) | 2005-02-03 |
| JP4824147B2 (ja) | 2011-11-30 |
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| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160919 |